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Blankcanvas is right, there are many different factors that would have to be right for pregnancy to happen. Precum can contain sperm, yes. You just finished your period so that means you are likely about to ovulate soon. Sperm can survive up to about 5 days. All these increase the chances of pregnancy.
I GUARANTEE your boyfriend has ejaculated within the last year. Even if he doesn't masturbate, unlikely for a 16 year old, he'd have nocturnal emissions (wet dreams). It really doesn't matter if it has been a year or not. If he HAS NOT ejaculated since the last time he urinated, chance of precum containing sperm are low - but they do exist.
Yes, having sex ANY time can hurt. It can hurt at any point when the penis enters the vagina. It depends upon the size of his penis, the size of your vagina, how lubricated you both are, how ready and relaxed you are. Remember, the muscles, tissues, etc, are not used to having a penis in them. Tissues tear, there can be some bleeding.
Always use protection, all the time.
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